Waterfront vacation rentals in Siesta Key

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Top-rated waterfront rentals in Siesta Key

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Siesta Key

4.97 out of 5 average rating, 37 reviews

2 BR condo in Siesta Key w/ Private beach access

Relax and enjoy your time at Siesta Key with private beach access and relaxing view of both the intercoastal and beach from the spacious balcony. Minutes away from the bars and old village. This thoughtfully remodeled 2 bedroom 2 bathroom condo is fully stocked with all your vacation needs including a washer and dryer for your private use. You will have access to in building amenities: Olympic size pool, Tennis court, Sauna, Excercise room, BBQs, Shuffleboard, Cover Parking, and a Boat Dock.

Sep 16 – 23

R4,255 ZAR per night

Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

*NEW May 17 CX 30% OFF! Sarasota #1 Luxury Villa*

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Nov 13 – 20

R11,649 ZAR per night

Guest favorite

Condo in Siesta Key

4.91 out of 5 average rating, 89 reviews

NO Stairs, beachfront & short walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

Sep 24 – Oct 1

R13,057 ZAR per night

Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 276 reviews

On the Beach; Siesta Key SunBum Studio

STEPS TO YOUR OWN PRIVATE BEACH!! NO TRICKS or GIMMICKS LIKE OTHER LISTINGS on the KEY. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, new gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking! You are sure to enjoy your time here on the #1 U.S. Beach.

Mar 4 – 11

R8,459 ZAR per night

Guest favorite

Condo in Siesta Key

5.0 out of 5 average rating, 18 reviews

Amazing beach view! Entire unit renovated!

The entire unit is completely renovated! Brand new furniture, appliances, and 2 55-inch smart TVs, etc. It comfortably sleeps 4 people. This 1 bedroom/1 bath unit include a California king bedroom set in the bedroom, queen and full sleeper sofas in the living room, and pack-n-play for infants. Big lanai area, enjoy amazing views of the ocean. This 3rd-floor unit steps away from #1 Siesta Key beach. This unit is a short distance to siesta key village for restaurants, shops, & entertainment.

Sep 19 – 26

R4,266 ZAR per night

Guest favorite

Tiny home in Sarasota

4.9 out of 5 average rating, 173 reviews

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

Jul 13 – 20

R3,152 ZAR per night

Superhost

Condo in Siesta Key

4.82 out of 5 average rating, 131 reviews

The Key to a Great Vacation!

Welcome to our one bedroom, one bath (4 piece) main floor condo. Recently renovated. Freshly painted with new furniture, a brand new king size memory foam mattress with contemporary decoration (with queen size pull out couch). Easily accessible with no steps to climb and close, convenient parking right outside the front door. Quiet, peaceful and near both Siesta Key Beach and the condo pool ensure a wonderful vacation. Walk across the street and enjoy one of the best beaches in the world.

Sep 18 – 25

R3,811 ZAR per night

Guest favorite

Apartment in Siesta Key

4.94 out of 5 average rating, 83 reviews

Siesta Premier Location - The 'Calm of Siesta'

My place is right across the street from Siesta Key beach, family-friendly activities, and nightlife. You’ll love my place because of the location, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, adventurers, business travelers, and families. Walking distance to the village and is at less crowded section of the public beach which equals perfect location!! Updated and beautifully decorated condo with breathtaking view of the beach, You will LOVE it!

Jul 6 – 13

R5,514 ZAR per night

Guest favorite

Condo in Longboat Key

4.93 out of 5 average rating, 145 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf of Mexico and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Nov 6 – 13

R5,680 ZAR per night

Guest favorite

Condo in Longboat Key

4.97 out of 5 average rating, 149 reviews

Charming Condo on the Coast!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with complimentary chairs and umbrellas. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

Nov 22 – 29

R5,841 ZAR per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 238 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

May 26 – 31

R2,322 ZAR per night

Superhost

Apartment in Siesta Key

5.0 out of 5 average rating, 6 reviews

Sunset Sensation

Come enjoy this beautiful end unit condo, over seeing unobstructed views of west coast Florida’s premier white sandy beaches. Amenities such as a gourmet kitchen with high-end appliances, modern furniture, and flat screen TVs throughout. Enjoy the wrap around patio and it’s views. Complex includes barbecue amenities on the ground floor free on site parking and easy access to the beach. All check in and check out procedures are provided in a binder in the unit upon arrival

Dec 2 – 9

R8,529 ZAR per night